Thomas Fitzpatrick and the drunk Marine who landed a stolen airplane on a New York City street twice

Thomas Fitzpatrick, a decorated Marine and Korean War veteran, twice stole single-engine airplanes from Teterboro, New Jersey, and landed them on a narrow Manhattan street in the middle of the night — once in 1956 and again in 1958 — both times to settle bar bets. Neither incident injured a single person on the ground or in the aircraft.

How Did a Drunk Marine Land an Airplane on a New York City Street?

In late September 1956, Fitzpatrick was drinking at a bar on Saint Nicholas Avenue in Washington Heights when someone claimed it was impossible to get from New Jersey to upper Manhattan in fifteen minutes at that hour. Fitzpatrick, with considerable whiskey and considerable flight experience, decided to prove them wrong.

He made his way to Teterboro Airport in the middle of the night, found an unguarded Stinson 108 on the ramp, climbed in, and took off. Airport security in 1956 was virtually nonexistent — a padlock on the fuel pump was considered thorough.

He flew the Stinson across the Hudson River, picked up Saint Nicholas Avenue, and set the airplane down on the street in front of the bar. Between parked cars and lamp posts. On pavement built for taxi cabs, not tailwheels. Then he walked back inside.

What Happened After the First Landing?

Police responded — an airplane on a city street is difficult to overlook. The aircraft’s owner pressed charges, and Fitzpatrick went before a judge who fined him one hundred dollars. That was the entire consequence for stealing an airplane and landing it on a Manhattan street.

Why Did Fitzpatrick Do It a Second Time?

In October 1958, Fitzpatrick was back in the same Washington Heights neighborhood, back in a bar, when someone questioned the original story. They said it never happened, that there was no way he had actually landed a plane on Saint Nicholas Avenue.

He repeated the entire sequence. He went to Teterboro, took a Cessna 140 without permission, flew it across the Hudson, and landed it on Saint Nicholas Avenue — one block from the first landing site — at 2:00 a.m.

The police were less forgiving the second time. A psychiatrist was brought in to evaluate him, and a judge sentenced Fitzpatrick to six months in jail — still a remarkably light sentence for a man who had now stolen two airplanes and landed both on city streets.

What Made These Landings So Extraordinary?

The illegality and recklessness are indefensible. But the airmanship involved was extraordinary by any standard.

Fitzpatrick took off from Teterboro in darkness with no flight plan, no clearance, and no GPS. Navigation was entirely visual — the grid of city lights, the dark stripe of the Hudson, and memory of which avenue ran which direction. He identified a street narrow enough that his wingspan barely cleared the parked cars on either side, judged his altitude, speed, and glide angle at night, and touched down between obstacles with zero margin for error.

Once he dropped below the rooftops on a street approach, there was no go-around. No missed approach procedure. The decision tree had exactly two branches: put the airplane on the ground, or put it into a building. He executed it cleanly both times.

He preflighted an unfamiliar airplane on a dark ramp, figured out where everything was, and flew it with enough precision to thread a corridor of lamp posts and fire hydrants. Had he applied those skills legally, he might have had a serious career as a bush pilot.

What Happened to Thomas Fitzpatrick?

Fitzpatrick reportedly said very little about either incident for the rest of his life. He passed away in 2009. The New York Times ran a short obituary mentioning the landings, introducing the story to a new generation.

Among pilots in northern New Jersey during the 1960s and 1970s, the story had already become legend — passed around like a worn sectional chart. Someone always knew someone who had been in the bar that night, or who had seen the airplane on the street the next morning, or who had worked the Teterboro ramp when police came asking questions.

Key Takeaways

Thomas Fitzpatrick landed stolen airplanes on a Manhattan street twice — in 1956 and 1958 — both times to win bar arguments
The first incident resulted in a $100 fine; the second earned him six months in jail
Both landings were executed at night with no instruments, no flight plan, and no margin for error on streets barely wider than the aircraft’s wingspan
Neither landing injured anyone, a testament to exceptional — if profoundly misguided — stick-and-rudder skill
The story, sourced from New York Times archives and FAA records, remains one of the most remarkable tales in general aviation history